Looking ahead to its 50th anniversary in 2020, the Martha’s Vineyard Chamber Music Society opened this year’s season with an ensemble that has already reached the half-century milestone. Infinity Brass was founded in 1968 when its five members were still music students. Now they are professors, acclaimed soloists and recording artists, located across the United States. When they gathered on Monday night at the Old Whaling Church, they played together with the ease of lifelong comrades.

Monday’s concert (set to repeat Tuesday evening at the Chilmark Community Center) took audience members on an all-terrain tour of brass repertoire from three centuries: the 18th (J.S. Bach and W.A. Mozart), 20th (Duke Ellington, Astor Piazzolla and Malcolm Arnold) and 21st (Damian Montano, born in 1976, and Kevin McKee, born in 1980).

Infinity Brass members took turns introducing the works.

The show opened on a dramatic note with Mr. McKee’s piece Escape, a suspenseful soundtrack to the West Coast composer’s rock-climbing pastime. Scaling the peaks and glissading down sudden slopes, Infinity Brass kept its footing throughout, skidding back to sea level in a blaze of trumpets. Tuba player Scott Watson told the audience that Escape is Mr. McKee’s very first composition for brass quintet.

The Piazzolla was next, a pulsing tango called Oblivion that could have accompanied the pivotal scene in a classic film noir. As its final notes faded in the hushed Whaling Church, a crash of bottles from across Church street added a hard-boiled postscript.

Christopher Moore on trumpet and Paul Stevens on French Horn. — Mark Alan Lovewell

Astor Piazzolla and Malcolm Arnold were born in the same year, 1921, and were both virtuosi on their instruments, but they pursued very different musical visions. Piazzolla played the concertina-like bandoneon and devoted his career to remaking traditional Argentine tango into a challenging contemporary music style. Arnold was a brilliant trumpeter and film composer — he earned an Oscar for scoring The Bridge on the River Kwai — who experimented with non-traditional instrumentation including vacuum cleaners, rifles and a floor polisher.

Written in 1961, Arnold’s Quintet for Brass No. 1 is a workout for the quintet, particularly the trumpeters, said Infinity Brass trumpeter Christopher Moore in his introduction.

“I think he was trying to torture us trumpet players as much as he could and still provide great entertainment for the audience,” Mr. Moore said.

The piece moves from a bright, almost martial Allegro Vivace to a slower, darker Chaconne, building a sense of urgency as individual players fired off brief, intense statements. The final movement, Con Brio, was a jazzy tally-ho of slides and quick starts and stops, especially for the trumpets.

Following intermission, the quintet delighted its Whaling Church audience with a pair of hits from the classical era: Bach’s Fugue in G. Minor, also known as “the Little” (Bach’s Fantasia and Fugue in G Minor is “the Great”). An organ work transcribed for brass, the fugue drew whoops of applause from listeners.

Wayne du Maine, principal trumpeter with the Brooklyn Philharmonic and American Composers Orchestra, introduced his arrangement of the rondo from Mozart’s Horn Concerto #4 in E flat major. Always a good time for listeners, this romp showcased the mastery of Infinity founder and horn player Paul Stevens, whose notes flowed as if effortlessly from one of the world’s most difficult musical instruments.

Andrew Malloy on trombone and Wayne du Maine on trumpet.

“Everybody loves Paul,” trombonist Andrew Molloy faux-grumped as the audience cheered. But with Damian Montano’s Four Plus One, it was Molloy’s turn in the musical spotlight. A member of the Los Angeles Chamber Orchestra, Mr. Montano wrote the quintet as a commission for Mr. Molloy and his Crown City Brass Quintet. It’s a diverse piece that moves from spiky and staccato to stately, with a surprise ending.

In another surprise, Infinity Brass inserted an extra piece of music that wasn’t included in the program.

“One thing brass has always done is play music for ceremonial events,” Mr. Stevens said. “Something about hearing it from brass instruments really goes to the heart.” The group then played the first verse and chorus from a gorgeously layered, contemporary arrangement of America the Beautiful.

Before the audience could respond, Mr. du Maine began snapping his fingers and the quintet launched into Duke Ellington’s Rent Party Blues, a snappy 1930 dance number that saw Mr. du Maine on his feet, aiming the bell of his golden horn high like Ellington’s own great trumpeter Cat Anderson. By the end of the song, the audience was on its feet as well in a standing ovation for Infinity Brass.

The Chamber Music Society’s summer festival continues through August 14 with a series of paired performances taking place at 8 p.m. on Mondays at the Old Whaling Church and Tuesdays at the Chilmark Community Center.

On July 23 and July 24, flutist Carol Wincenc appears with Andy Lin on viola and the society’s artistic director Delores Stevens on piano, in a program of music by Jean Sibelius, François Devienne, Francis Poulenc, Ernest Bloch, Maurice Duruflé, concluding with The Wildlife Suite by Tien-Hua Liu and Yao-Xing Chen.

Ms. Stevens performs an all-classics with violinist Gary Levinson, violist Michael Klotz and cellist Jason Calloway on July 30 and July 31: Mozart’s Duo for Violin and Viola in G Major, Beethoven’s String Trio in E Flat Major, Op. 3 and Robert Schumann’s Piano Quartet in E Flat Major, Opus 47.

On August 6 and August 7, the Martha’s Vineyard Piano Quartet returns for its annual engagement with Ms. Stevens on piano, Stephanie Chase on violin, Scott Woolweaver on viola and Jan Müller-Szeraw on cello. They will play works by Clara Schumann, York Bowen and Gabriel Fauré.

The festival wraps up August 13 and August 14 with the trio of Diana Cohen on violin, Franklin Cohen on clarinet and Roman Rabinovich on piano, playing the music of Joseph Haydn, John Adams, Robert Schumann, Poulenc and Béla Bartók.

This Sunday, July 22, the festival is holding its first-ever gala benefit concert at 7 p.m. in the Old Whaling Church. Titled Brio, Bliss, Boffo: Celebrating Music Through Song, the show features seven singers including Island favorites David Behnke, Molly Conole and Jenny Friedman alongside Metropolitan Opera soloists who are on the Island for next weekend’s Opera at Featherstone. There will also be four pianists: Peter Boak, Philip Dietterich, Ed Bak and Molly Sturges. Actor Donovan Dietz will narrate.

Tickets are $25 to benefit the chamber music society, which in addition to producing the summer festival provides instruments and support to young musicians in Island schools. Higher patron admission levels are also available for those who would like to contribute a greater amount.

For more information, visit mvcms.org.